Seriously, it's been sooo long since a game made me laugh as hard as the play scene in Tales of Graces F. So much awesome. You could tell the VA's had fun with it too, something about the way Cheria says "YYEEEESSS" had me dying.

Almost any of the side quests in Shadow Hearts 2 or 3. That game had some very entertaining ones, like Joachim and the hundred battles tower. Always good fun. :)

I never really liked hundred battle towers or similar endurance challenges since those always force you to burn about half an hour's worth of time on fodder and the end of the dungeon is usually loaded with enemies ready to one shot your ass forcing you to repeat the entire process all over again.